Hydrochloric Acid → 2-(4-Chlorophenyl)-2-methylpropanal

HRID 610845Notes

Reaction equation

HRID 610845 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([CH3:20])([CH3:19])[C:17]#N)=[CH:14][CH:13]=1.[OH2:23].Cl>CCCCCC.C(OCC)C>[Cl:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([CH3:20])([CH3:19])[CH:17]=[O:23])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 101302194-Chloro-α,α-dimethylbenzeneacetonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 114353342-(4-Chlorophenyl)-2-methylpropanalYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

Diisobutylaluminum hydride (0.236 mol, 236 mL of a 1M solution in hexane) is added over 90 minutes to a solution of p-chloro-α-methylhydratroponitrile (32.6 g, 0.181 mol) in diethyl ether under nitrogen at 0° C. After the addition is complete, water and 6N hydrochloric acid are added to the reaction mixture while maintaining the temperature below 30° C. The resultant aqueous solution is stirred overnight at room temperature and extracted with diethyl ether The organic extracts are combined, washed sequentially with 2N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as an oil (31.1 g, 94% yield).

Workup

  1. additionAfter the addition
  2. temperaturewhile maintaining the temperature below 30° C
  3. extractionextracted with diethyl ether The organic extracts
  4. washwashed sequentially with 2N hydrochloric acid and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2550eb0f5fe74f7397ad3bb2d8d74d35
Source dataset
uspto-grants-1999_12
Patent number
US05998673

Reaction notes

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